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Chapter 14: Q6P (page 527)

Question: Label the protons in each highlighted \({\bf{C}}{{\bf{H}}_{\bf{2}}}\) group as enantiotopic, diastereotopic, or homotopic.

a.

b.

c.

Short Answer

Expert verified

  1. Enantiotopic

  2. Neither

  3. Diastereotopic

Step by step solution

01

Homotopic, enantiotopic, and diastereotopic protons

  • Homotopic protons are formed when the same product is formed by the substitution of two H by Z.
  • Enantiotopic protons are formed when two H are equivalent and occur at the same NMR signal.
  • Diastereotopic protons are formed when two H are not equivalent and occur at two different signals.
02

Explanation for highlighted proton

a.

The replacement of H with X is shown below.

Enantiotopic proton

b.

The replacement of H with X is shown below.

Neither enantiotopic nor diastereotopic

c.

The replacement of H with X is shown below.

Diastereotopic proton

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Most popular questions from this chapter

The reaction of (CH3)3 CCHO with (C6H5)3 P=C(CH3)OCH3 , followed by treatment with aqueous acid, afford R . R has strong absorption in its IR spectrum at 1717 cm-1 and three singlets in its -NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 21.

Which of the highlighted carbon atoms in each molecule absorbs farther downfield?

a.

b.

c.

d.

Compound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate and which compound corresponds to ethylene diacetate?

Draw the four constitutional isomers having molecular formula \({{\bf{C}}_{\bf{4}}}{{\bf{H}}_{\bf{9}}}{\bf{Br}}\) and indicate how many different kinds of carbon atoms each has.

Question: How many \(^{\bf{1}}{\bf{H}}\) NMR signals does each compound give?

a.

b.

c.

d.

See all solutions

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